Aluminum(III) Chloride → HCID 66987441, compound

HRID 555724Notes

Reaction equation

HRID 555724 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]2[N:22]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[CH:23]=[N:24][C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=[C:16]([Cl:40])[CH:15]=3)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:40][C:16]1[CH:15]=[C:14]2[C:19]([C:20]([C:21]3[N:22]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[CH:23]=[N:24][C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:12]([CH2:10][NH:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[NH:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 56951871HCID 56951871, compound

Product 1

HCID 66987441HCID 66987441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 2 (101 mg, 0.18 mmol), AlCl3 (117 mg, 0.88 mmol) and LAH (33 mg, 0.88 mmol) in THF (2 mL) is refluxed. After completion the reaction mixture is quenched by sodium-potassium tartarate and neutralized by saturated aqueous NaHCO3. EtOA is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; ES-MS: M+H=561.8: AtRet=3.74 min.

Workup

  1. customAfter completion the reaction mixture is quenched by sodium-potassium tartarate
  2. additionEtOA is added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-751db3a92a4b460b8c959060e4957929
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

Loading…